3981. Fenoterol

Nomenclature

CAS number: 13392-18-2
5-[1-Hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-1,3-benzenediol; 3,5-dihydroxy-α-[[(p-hydroxy-α-methylphenethyl)amino]methyl]benzyl alcohol; 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-[(4-hydroxyphenyl)isopropylamino]ethane; 1-(p-hydroxyphenyl)-2-[[β-hydroxy-β-(3′,5′-dihydroxyphenyl)]ethyl]aminopropane; TH-1165.
C17H21NO4; mol wt 303.35.
C 67.31%, H 6.98%, N 4.62%, O 21.10%.

Description and references

β2-Adrenergic agonist. Prepn and sepn of stereoisomers: BE 640433; Zelle et al., US 3341593 (1962, 1967 to Boehringer, Ing.). Pharmacology: Schuster, Baum, Arzneim.-Forsch. 19, 1905 (1969); O'Donnell, Eur. J. Pharmacol. 12, 35 (1970). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Metabolism in mice: S. Kojima et al., Arzneim.-Forsch. 30, 959 (1980). HPLC determn in plasma: S. Kramer, G. Blaschke, J. Chromatogr. B 751, 169 (2001). Clinical evaluation: Tweel, Ann. Allergy 29, 142 (1971); Rebuck, Saunders, Med. J. Aust. 1, 225 (1972). Comparison with ritodrine in preterm labor: J. Gerris et al., Eur. J. Clin. Pharmacol. 18, 443 (1980). Review of pharmacology and therapeutic efficacy: R. C. Heel et al., Drugs 15, 3-32 (1978); N. Svedmyr, Pharmacotherapy 5, 109-126 (1985).

Chemical structure

Derivative

Hydrobromide.

Nomenclature

CAS number: 1944-12-3
TH-1165a; Airum (Promeco); Berotec (Boehringer, Ing.); Dosberotec (Boehringer, Ing.); Partusisten (Boehringer, Ing.).
C17H21NO4.HBr; mol wt 384.26.
C 53.14%, H 5.77%, N 3.65%, O 16.65%, Br 20.79%.

Properties

Crystals from methanol-ether, mp 222-223°. LD50 in mice (mg/kg): 1100 s.c.; 1990 orally (Goldenthal).

Derivative

Hydrochloride.

Nomenclature

CAS number: 1944-10-1
C17H21NO4.HCl; mol wt 339.81.
C 60.09%, H 6.53%, N 4.12%, O 18.83%, Cl 10.43%.

Properties

mp 183° (acetonitrile-ether).

Therapeutic Category

Bronchodilator; tocolytic.

Keywords

β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives; Tocolytic